The present invention relates to oxime compounds, their use, and intermediates for their production.
As disclosed, for example, in JP-A61-72733 and JP-A61-260054, it is well known that certain types of oxime compounds can be used as the active ingredients of insecticides. These compounds are, however, not necessarily satisfactory for the active ingredients of insecticidal/acaricidal agents in view of their insecticidal activity.
Under these circumstances, the present inventors have extensively studied to find out compounds with excellent insecticidal/acaricidal activity. As a result, they have found that oxime compounds of formula (1) as depicted below have excellent insecticidal/acaricidal activity, thereby completing the present invention.
Thus, the present invention provides oxime compounds of formula (1)

(hereinafter referred to as the present compound(s))
wherein:
R1, R2, and R3 are independently halogen, C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C1-C3 haloalkoxy, nitro, or cyano;
R4 is 3,3-dihalogeno-2-propenyl;
a is an integer of 0 to 2;
Y is oxygen, sulfur, or NH;
Z is oxygen, sulfur, or NR5 wherein R5 is hydrogen, acetyl, or C1-C3 alkyl;
X is X1 or X2 of formula (2)

xe2x80x83wherein:
R6 is hydrogen, C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, or triphenylmethyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C1-C6 alkyl substituted with cyano, nitro, (C1-C4 alkoxy)-carbonyl, C1-C4 alkylthio, or C1-C4 alkoxy,
or T1-1, T1-2, T1-3, T1-4, T1-5, T1-6, or T1-7 of formula (3)

xe2x80x83wherein:
(R10)b""s are zero to five identical or different substituents selected from halogen, C1-C6 alkyl, C1-C3 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C3 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, (C1-C5 alkoxy)carbonyl, cyano, or nitro;
R11, R12, R13, and R14 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
D is xe2x80x94CHxe2x95x90 or nitrogen;
J is oxygen or sulfur;
b is an integer of 0 to 5;
d is an integer of 1 to 3;
e is an integer of 0 to 3;
f is an integer of 2 to 4;
R15 is C1-C6 alkyl, C1-C3 haloalkyl, C2-C6 alkenyl, or C3-C6 cycloalkyl,
or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, or C1-C3 haloalkoxy; and
R16 and R42 are independently C1-C6 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, C3-C6 haloalkynyl, or C3-C6 cycloalkyl,
or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, or C1-C3 haloalkoxy,
or benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C4 alkoxy, or C1-C3 haloalkoxy on the ring thereof;
R7 is hydrogen, C1-C6 alkyl, C1-C3 haloalkyl, C3-C6 cycloalkyl, cyano, cyano C1-C3 alkyl, (C1-C4 alkoxy)carbonyl, or (C1-C4 alkoxy)-carbonyl(C1-C3)alkyl,
or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy,
or benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof;
R8 and R9 are independently hydrogen, C1-C11 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C10 alkoxyalkyl, C2-C10 alkylthioalkyl, or naphthyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 on the ring thereof,
or T2-1 or T2-2 of formula (4)

xe2x80x83wherein:
(R7)b""s are zero to five identical or different substituents selected from halogen, C1-C6 alkyl, C1-C3 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C3 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 haloalkylsulfinyl, C1-C2 haloalkylsulfonyl, C1-C3 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, dimethylamino, acetamido, acetyl, formyl, carboxyl, (C1-C2 alkyl)aminocarbonyl, [di(C1-C2 alkyl)amino]carbonyl, (C1-C6 alkoxy)carbonyl, C3-C6 cycloalkyl, C5-C6 cycloalkenyl, C3-C6 cycloalkyloxy, C5-C6 cycloalkenyloxy, pentafluorosulfanyl (F5S), cyano, or nitro,
or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy,
or phenoxy optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy,
or benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof,
or benzyloxy optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof,
or when b is 2 to 5, two adjacent R17""s are combined together at their ends to form trimethylene or tetramethylene,
or when b is 2 to 5, two adjacent R17""s are combined together at their ends to form methylenedioxy optionally substituted with halogen or C1-C3 alkyl,
or when b is 2 to 5, two adjacent R17""s are combined together at their ends to form ethylenedioxy optionally substituted with halogen or C1-C3 alkyl;
D is xe2x80x94CHxe2x95x90 or nitrogen;
R11 and R12 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
b is an integer of 0 to 5; and
d is an integer of 1 to 3;
or a heterocyclic group, exclusive of pyridine ring, which heterocyclic group may be optionally substituted with one to three identical or different (R18)g""s,
wherein:
R18 is halogen, C1-C6 alkyl, C1-C3 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C3 haloalkoxy, C3-C6 alkenyloxy, C3-C6 haloalkenyloxy, C3-C6 alkynyloxy, C3-C6 haloalkynyloxy, C1-C3 alkylthio, C1-C3 haloalkylthio, C1-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 haloalkylsulfinyl, C1-C2 haloalkylsulfonyl, C1-C3 hydroxyalkyl, C2-C4 alkoxyalkyl, C2-C4 alkylthioalkyl, cyano, or nitro,
or phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy; and
g is an integer of 1 to 3;
or R8 and R9 are combined together at their ends to form a saturated or unsaturated 5- or 6-membered ring containing zero to two oxygen or sulfur atoms in the ring;
A1 is A1-1, A1-2, A1-3, A1-4, A1-5, A1-6, A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12 of formula (5)
A1-1: xe2x80x94(CR19xe2x95x90CR20)hxe2x80x94(CR21R22)ixe2x80x94
A1-2: xe2x80x94(CR19xe2x95x90CR20)hxe2x80x94(CR21R22)jxe2x80x94Q1xe2x80x94(CR23R24)kxe2x80x94
A1-3: xe2x80x94(CR19xe2x95x90CR20)hxe2x80x94(CR21R22)jxe2x80x94Q1xe2x80x94(CR23R24)mxe2x80x94CR25xe2x95x90CR26xe2x80x94(CR27R28)nxe2x80x94
A1-4: xe2x80x94(CR19xe2x95x90CR20)hxe2x80x94(CR21R22)jxe2x80x94Q1xe2x80x94(CR23R24)mxe2x80x94Cxe2x89xa1Cxe2x80x94(CR25R26)nxe2x80x94
A1-5: xe2x80x94(CR19xe2x95x90CR20)hxe2x80x94(CR21R22)jxe2x80x94Q1xe2x80x94(CR23R24)pxe2x80x94Exe2x80x94(CR25R26)qxe2x80x94
A1-6: xe2x80x94(CR19xe2x95x90CR20)hxe2x80x94(CR21R22)jxe2x80x94Q1xe2x80x94(CR23R24)rxe2x80x94Q2xe2x80x94(CR25R26)sxe2x80x94
A1-7: xe2x80x94U1xe2x80x94(CR19R20)txe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)uxe2x80x94(CR27xe2x95x90CR28)pxe2x80x94(CR29R30)jxe2x80x94
A1-8: xe2x80x94U2xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)uxe2x80x94(CR27xe2x95x90CR28)pxe2x80x94(CR29R30)vxe2x80x94
A1-9: xe2x80x94U1xe2x80x94(CR19R20)txe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)jxe2x80x94Q1xe2x80x94(CR27R28)vxe2x80x94(CR29xe2x95x90CR30)pxe2x80x94(CR31R32)wxe2x80x94
A1-10: xe2x80x94U2xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)vxe2x80x94Q1xe2x80x94(CR27R28)wxe2x80x94(CR29xe2x95x90CR30)pxe2x80x94(CR31R32)xxe2x80x94
A1-11: xe2x80x94U1xe2x80x94(CR19R20)txe2x80x94Q1xe2x80x94(CR23R24)hxe2x80x94Exe2x80x94(CR25R26)pxe2x80x94
A1-12: xe2x80x94U1xe2x80x94(CR19R20)txe2x80x94Q1xe2x80x94(CR23R24)jxe2x80x94Cxe2x89xa1C(CR25R26)mxe2x80x94
wherein:
R19, R20, R21, R23, R24, R25, R26, R27, R28, R29, R30, R31, and R32 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
R22 is hydrogen, C1-C3 alkyl, or trifluoromethyl,
or when h is 0 and i is 1 in A1-1, R22 and R7 may be combined together at their ends to form trimethylene, tetramethylene, or pentamethylene, each of which may be optionally substituted with C1-C3 alkyl,
or when h is 0 and j is 1, in A1-2, A1-3, A1-4, A1-5, or A1-6, R22 and R7 may be combined together at their ends to form trimethylene, tetramethylene, or pentamethylene, each of which may be optionally substituted with C1-C3 alkyl;
h is an integer of 0 or 1;
i is an integer of 1 to 6;
j is an integer of 1 to 3;
k is an integer of 2 to 8;
m is an integer of 1 to 3;
n is an integer of 1 to 3;
p is an integer of 0 or 1;
q is an integer of 0 or 1;
r is an integer of 2 to 4;
s is an integer of 2 to 4;
t is an integer of 0 to 3;
u is an integer of 0 to 3;
v is an integer of 1 to 4;
w is an integer of 1 to 4;
x is an integer of 1 to 4;
Q1 is oxygen, S(O)y, or NR33 wherein R33 is hydrogen or C1-C3 alkyl, and y is an integer of 0 to 2;
Q2 is oxygen, S(O)z, or NR34 wherein R34 is hydrogen or C1-C3 alkyl, and z is an integer of 0 to 2;
E is C5-C6 cycloalkylene;
U1 is U1 of formula (6)
xe2x80x94G1xe2x80x94Wxe2x80x94
xe2x80x83wherein:
W is an optionally substituted benzene ring or an optionally substituted heterocyclic ring;
G1 is G1-1 or G1-2 of formula (7)
G1-1: xe2x80x94(CR35R36)a1xe2x80x94
G1-2: xe2x80x94(CR35R36)b1xe2x80x94Q2xe2x80x94(CR37R38)d1
xe2x80x83wherein:
Q2 is oxygen, S(O)z, or NR34 wherein R34 is hydrogen or C1-C3 alkyl, and z is an integer of 0 to 2;
R35, R36, R37 and R38 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
a1 is an integer of 0 to 4;
b1 is an integer of 1 to 3; and
d1 is an integer of 0 to 2;
U2 is U2 of formula (8)
xe2x80x94G1xe2x80x94Wxe2x80x94G2xe2x80x94
xe2x80x83wherein:
W is an optionally substituted benzene ring or an optionally substituted heterocyclic ring;
G1 is G1-1 or G1-2 of formula (7)
G1-1: xe2x80x94(CR35R36)a1xe2x80x94
G1-2: xe2x80x94(CR35R36)b1xe2x80x94Q2xe2x80x94(CR37R38)d1
xe2x80x83wherein:
Q2 is oxygen, S(O)z, or NR34 wherein R34 is hydrogen or C1-C3 alkyl, and z is an integer of 0 to 2;
R35, R36, R37, and R38 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
a1 is an integer of 0 to 4;
b1 is an integer of 1 to 3; and
d1 is an integer of 0 to 2; and
G2 is oxygen, S(O)e1, or NR39 wherein R39 is hydrogen or C1-C3 alkyl, and e1 is an integer of 0 to 2;
A2 is A2-1, A2-2, A2-3, A2-4, A2-5, A2-6, A2-7, A2-8, A2-9, or A2-10 of formula (9)
A2-1: xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)txe2x80x94(CR27xe2x95x90CR28)pxe2x80x94(CR29R30)mxe2x80x94
A2-2: xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)mxe2x80x94Q1xe2x80x94(CR27R28)nxe2x80x94(CR29xe2x95x90GR30)pxe2x80x94(CR31R32)f1xe2x80x94
A2-3: xe2x80x94U3xe2x80x94(CR19R20)txe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)uxe2x80x94(CR27xe2x95x90CR28)pxe2x80x94(CR29R30)jxe2x80x94
A2-4: xe2x80x94U4xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)txe2x80x94(CR27xe2x95x90CR28)pxe2x80x94(CR29R30)mxe2x80x94
A2-5: xe2x80x94U3xe2x80x94(CR19R20)txe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)jxe2x80x94Q1xe2x80x94(CR27R28)mxe2x80x94(CR29xe2x95x90CR30)pxe2x80x94(CR31R32)nxe2x80x94
A2-6: xe2x80x94U4xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)mxe2x80x94Q1xe2x80x94(CR27R28)nxe2x80x94(CR29xe2x95x90CR30)pxe2x80x94(CR31R32)f1xe2x80x94
A2-7: xe2x80x94U3xe2x80x94(CR19R20)txe2x80x94Q1xe2x80x94(CR23R24)hxe2x80x94Exe2x80x94(CR25R26)pxe2x80x94
A2-8: xe2x80x94U3xe2x80x94(CR19R20)txe2x80x94Q1xe2x80x94(CR23R24)jxe2x80x94Cxe2x89xa1Cxe2x80x94(CR25R26)mxe2x80x94
A2-9: xe2x80x94(CR19R20)hxe2x80x94Exe2x80x94(CR23R24)pxe2x80x94
A2-10: xe2x80x94(CR19R20)jxe2x80x94Cxe2x89xa1Cxe2x80x94(CR23R24)mxe2x80x94
wherein:
R19, R20, R23, R24, R25, R26, R27, R28, R29, R30, R31, and R32 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
h is an integer of 0 or 1;
j is an integer of 1 to 3;
m is an integer of 1 to 3;
n is an integer of 1 to 3;
p is an integer of 0 or 1;
t is an integer of 0 to 3;
u is an integer of 0 to 3;
f1 is an integer of 1 to 3;
Q1 is oxygen, S(O)y, or NR33 wherein R33 is hydrogen or C1-C3 alkyl, and y is an integer of 0 to 2;
E is C5-C6 cycloalkylene;
U3 is U3-1, U3-2, or U3-3 of formula (10)

xe2x80x83wherein:
R35 and R36 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
(R40)g1""s are zero to four identical or different substituents selected from halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy;
R and V are independently xe2x80x94CHxe2x95x90 or nitrogen;
g1 is an integer of 0 to 4;
h1 is an integer of 1 to 3;
i1 is an integer of 2 or 3; and
Q2 is oxygen, S(O)z, or NR34 wherein R34 is hydrogen or C1-C3 alkyl, and z is an integer of 0 to 2;
U4 is U4-1, U4-2, or U4-3 of formula (11)

xe2x80x83wherein:
R35 and R36 are independently hydrogen, C1-C3 alkyl, or trifluoromethyl;
(R40)g1""s are zero to four identical or different substituents selected from halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy;
R and V are independently xe2x80x94CHxe2x95x90 or nitrogen;
g1 is an integer of 0 to 4;
h1 is an integer of 1 to 3;
i1 is an integer of 2 or 3;
Q2 is oxygen, S(O)z, or NR34 wherein R34 is hydrogen or C1-C3 alkyl, and z is an integer of 0 to 2; and
Q3 is oxygen, S(O)e1, or NR39 wherein R39 is hydrogen or C1-C3 alkyl, and e1 is an integer of 0 to 2;
and insecticidal/acaricidal agents containing them as active ingredients.
In particular, the oxime compounds of formula (1) wherein X is X1 and R6 is hydrogen are useful both as the active ingredients of insecticidal/acaricidal agents and as the intermediates for the production of these active ingredient compounds.
The present invention further provides hydroxylamine compounds of formula (12)

wherein R1, R2, R3, R4, a, Y, Z, and A2 are as defined above, and salts thereof (e.g., inorganic acid salts such as hydrochlorides, sulfates, and nitrates).
The present invention further provides compounds of formula (13)

wherein R2, R3, R7, R19, R20, and j are as defined above, and R41 is 3,3-di-chloro-2-propenyl, 3,3-dibromo-2-propenyl, or 3-bromo-3-chloro-2-propenyl, which are useful as the intermediates for the production of the present compounds.
The present invention further provides compounds of formula (14)

wherein R2, R3, R7, R19, R20, R29, R30, R41, j, and v are as defined above, which are useful as the intermediates for the production of the present compounds.
The present invention further provides phenol compounds of formula 50)

wherein R1, R2, R3, a, X, and Z are as defined above, with the proviso that when X is X1, R6 is not hydrogen, which are useful as the intermediates for the production of the present compounds.
The halogen represented by R1, R2, R3, R10, R17, R18, or R40 may include fluorine, chlorine, bromine, and iodine.
The C1-C3 alkyl represented by R1, R2, R3, R5, R11, R12, R13, R14, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29, R30, R31, R32, R33, R34, R35, R36, R37, R38, or R39 may include methyl, ethyl, n-propyl, and isopropyl.
The C1-C8 alkyl represented by R6 may include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpropyl, n-hexyl, isohexyl, 2-ethyl-butyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl, 1,3-dimethylbutyl, n-heptyl, 1-ethyl-1-methylbutyl, n-octyl, and 1-methylheptyl.
The C1-C6 alkyl represented by R7, R10, R15, R16, R42, R17, or R18 may include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpropyl, n-hexyl, isohexyl, 2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl, and 1,3-dimethylbutyl.
The C1-C11 alkyl represented by RS or R9 may include, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpropyl, n-hexyl, isohexyl, 2-ethylbutyl, 1-methylpentyl, 1-ethylbutyl, 3-methylpentyl, 1,3-dimethyl-butyl, n-heptyl, 1-ethyl-1-methylbutyl, n-octyl, 1-methylheptyl, n-nonyl, n-decyl, and n-undecyl.
The C1-C4 alkyl represented by R40 may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.
The C1-C3 haloalkyl represented by R1, R2, R3, R7, R10, R15, R17, R18, or R40 may include, for example, trifluoromethyl, difluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, perfluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2-iodopropyl, and 2,3-dibromopropyl.
The C2-C6 haloalkyl represented by R6, R16, or R42 may include, for example, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2-iodopropyl, 2,3-dibromopropyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, 4-iodobutyl, 3-chloro-2,2-dimethylpropyl, 3-bromo-2,2-dimethylpropyl, 2,2,3,3,4,4,5,5-octafluoropentyl, 6-chlorohexyl, and 6-bromohexyl.
The C1-C6 haloalkyl represented by R8 or R9 may include, for example, trifluoromethyl, trichloromethyl, difluoromethyl, bromodifluoromethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2-iodopropyl, 2,3-dibromopropyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, 4-iodobutyl, 3-chloro-2,2-dimethylpropyl, 3-bromo-2,2-dimethylpropyl, 2,2,3,3,4,4,5,5-octafluoropentyl, 6-chlorohexyl, and 6-bromohexyl.
The C1-C3 alkoxy represented by R1, R2, R3, or R40 may include methoxy, ethoxy, n-propyloxy, and isopropyloxy.
The C1-C6 alkoxy represented by R10, R17, and R18 may include, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, 1-ethylpropyloxy, n-hexyloxy, isohexyloxy, 2-ethylbutyloxy, 1-methylpentyloxy, 1-ethylbutyloxy, 3-methylpentyloxy, and 1,3-diemthylbutyloxy.
The C1-C3 haloalkoxy represented by R1, R2, R3, R10, R17, R18, or R40 may include, for example, trifluoromethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 1-chloroethoxy, 1-bromoethoxy, perfluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxyethoxy, 2,2,2-tribromoethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2-dichloroethoxy, 2,2-dibromoethoxy, 3-fluoropropyloxy, 3-chloropropyloxy, 3-bromopropyloxy, 3-iodopropyloxy, 3,3,3-trifluoropropyloxy, 2,2,2,3,3,3-hexafluoropropyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2-fluoropropyloxy, 2-chloropropyloxy, 2-bromopropyloxy, 2-iodopropyloxy, and 2,3-dibromopropyloxy.
The C3-C6 alkenyl represented by R6, R16, or R42 may include, for example, allyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, and 4-methyl-4-pentenyl.
The C3-C6 haloalkenyl represented by R6, R16, or R42 may include, for example, 3-chloro-2-propenyl, 3-bromo-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 2-chloromethyl-2-propenyl, 4-chloro-2-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, 3-bromo-4,4,4-trifluoro-2-butenyl, 3,4-dichloro-4,4-difluoro-2-butenyl, 3,4,4,4-tetrafluoro-3-butenyl, 4,4-dichloro-3-butenyl, 4,4-dibromo-3-butenyl, 5,5-dichloro-4-pentenyl, 5,5,-dibromo-4-pentenyl, 6,6-dichloro-5-hexenyl, and 6,6-dibormo-5-hexenyl.
The C3-C6 alkynyl represented by R6, R16, or R42 may include, for example, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, and 2-ethyl-3-butynyl.
The C3-C6 haloalkynyl represented by R6, R16, or R42 may include, for example, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 4-chloro-2-butynyl, 4-chloro-3-butynyl, 4-bromo-2-butynyl, 4-bromo-3-butynyl, 5-chloro-4-pentynyl, 4-chloro-1-methyl-2-butynyl, 4-chloro-1-methyl-3-butynyl, 4-chloro-2-methyl-3-butynyl, 5-bromo-4-pentynyl, 4-bromo-1-methyl-2-butynyl, 4-bromo-1-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 6-chloro-5-hexynyl, and 6-bromo-5-hexynyl.
The C2-C6 alkenyl R8, R9, R10, R15, R17, or R18 may include, for example, vinyl, 1-propenyl, isopropenyl, 1-butenyl, allyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1-ethyl-2-propenyl, 2-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, and 4-methyl-4-pentenyl.
The C2-C6 haloalkenyl represented by R8, R9, R10, R17, or R18 may include, for example, 2-chloroethenyl, 2-bromoethenyl, 2,2-dichloroethenyl, 2,2-dibromoethenyl, 3-chloro-2-propenyl, 3-bromo-2-propenyl, 2-chloro-2-propenyl, 2-bromo-2-propenyl, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3,3-difluoro-2-propenyl, 2,3-dichloro-2-propenyl, 2,3-dibromo-2-propenyl, 2-chloromethyl-2-propenyl, 4-chloro-2-butenyl, 3-chloro-4,4,4-trifluoro-2-butenyl, 3-bromo-4,4,4-trifluoro-2-butenyl, 3,4-dichloro-4,4-difluoro-2-butenyl, 3,4,4,4-tetrafluoro-2-butenyl, 4,4-dichloro-3-butenyl, 4,4-dibromo-3-butenyl, 5,5-dichloro-4-pentenyl, 5,5-dibromo-4-pentenyl, 6,6-dichloro-5-hexenyl, and 6,6-dibromo-5-hexenyl.
The C2-C6 alkynyl represented by R8, R9, R10, R17, or R18 may include, for example, ethynyl, 1-propynyl, 1-butynyl, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, and 2-methyl-3-butynyl.
The C2-C6 haloalkynyl represented by R8, R9, R10, R17, or R18 may include, for example, 2-chloroethynyl, 2-bromoethynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 4-chloro-2-butynyl, 4-chloro-3-butynyl, 4-bromo-2-butynyl, 4-bromo-3-butynyl, 5-chloro-4-pentynyl, 4-chloro-1-methyl-2-butynyl, 4-chloro-1-methyl-3-butynyl, 4-chloro-2-methyl-3-butynyl, 5-bromo-4-pentynyl, 4-bromo-1-methyl-2-butynyl, 4-bromo-1-methyl-3-butynyl, 4-bromo-2-methyl-3-butynyl, 6-chloro-5-hexynyl, and 6-bromo-5-hexynyl.
The C3-C6 cycloalkyl represented by R7, R15, R16, R17, or R42 may include cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
The C2-C10 alkoxyalkyl represented by R8 or R9 may include, for example, methoxymethyl, ethoxymethyl, n-propyloxymethyl, isopropyloxymethyl, 2-methoxyethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl, 2-methoxy-1-methylethyl, 2-propyloxyethyl, 2-isopropyloxyethyl, 2-ethoxypropyl, 2-ethoxy-1-methylethyl, 2-methoxybutyl, 1-ethyl-2-methoxyethyl, 3-ethoxypropyl, 3-methoxybutyl, 3-methoxy-2-methylpropyl, 3-methoxy-1-methylpropyl, 2-butoxyethyl, 3-methoxy-3-methylbutyl, and 2-butoxy-1-methylethyl.
The C2-C10 alkylthioalkyl represented by R8 or R9 may include, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 2-methylthiomethyl, 1-methylthioethyl, 2-ethylthioethyl, 1-ethylthioethyl, 3-methylthiopropyl, 2-methylthiopropyl, 1-methylthiopropyl, 2-methylthio-1-methylethyl, 2-propylthioethyl, 2-isopropylthioethyl, 2-ethylthiopropyl, 2-ethylthio-1-methylethyl, 2-methylthiobutyl, 1-ethyl-2-methylthioethyl, 3-ethylthiopropyl, 3-methylthiobutyl, 2-methyl-3-methylthiopropyl, 1-methyl-3-methylthiopropyl, 4-methylthiobutyl, 1-methyl-2-methylthiopropyl, 2-isobutylthioethyl, 2-sec-butylthioethyl, 3-isobutylthiopropyl, and 3-sec-butylthiopropyl.
The C3-C6 alkenyloxy represented by R10, R17, or R18 may include, for example, allyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyloxy, 3-pentenyloxy, 4-pentenyloxy, 1-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy, 1-ethyl-2-propenyloxy, 2-ethyl-2-propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, and 4-methyl-4-pentenyloxy.
The C3-C6 haloalkenyloxy represented by R10, R17, or R18 may include, for example, 3-chloro-2-propenyloxy, 3-bromo-2-propenyloxy, 2-chloro-2-propenyloxy, 2-bromo-2-propenyloxy, 3,3-dichloro-2-propenyloxy, 3,3-dibromo-2-propenyloxy, 3,3-difluoro-2-propenyloxy, 2,3-dichloro-2-propenyloxy, 2,3-dibromo-2-propenyloxy, 2-chloromethyl-2-propenyloxy, 4-chloro-2-butenyloxy, 3-chloro-4,4,4-trifluoro-2-butenyloxy, 3-bromo-4,4,4-trifluoro-2-butenyloxy, 3,4-dichloro-4,4-difluoro-2-butenyloxy, 3,4,4,4-tetrafluoro-2-butenyloxy, 4,4-dichloro-3-butenyloxy, 4,4-dibromo-3-butenyloxy, 5,5-dichloro-4-pentenyloxy, 5,5-dibromo-4-pentenyloxy, 6,6-dichloro-5-hexenyloxy, and 6,6-dibrmo-5-hexenyloxy.
The C3-C6 alkynyloxy represented by R10, R17, or R18 may include, for example, 2-propynyloxy, 2-butynyloxy, 3-butynyloxy, 1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy, 3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-ethyl-2-butynyloxy, 1-ethyl-3-butynyloxy, and 2-ethyl-3-butynyloxy.
The C3-C6 haloalkynyloxy represented by R10, R17, or R18 may include, for example, 3-chloro-2-propynyloxy, 3-bromo-2-propynyloxy, 4-chloro-2-butynyloxy, 4-chloro-3-butynyloxy, 4-bromo-2-butynyloxy, 4-bromo-3-butynyloxy, 5-chloro-4-pentynyloxy, 4-chloro- 1-methyl-2-butynyloxy, 4-chloro-1-methyl-3-butynyloxy, 4-chloro-2-methyl-3-butynyloxy, 5-bromo-4-pentynyloxy, 4-bromo-1-methyl-2-butynyloxy, 4-bromo-1-methyl-3-butynyloxy, 4-bromo-2-methyl-3-butynyloxy, 6-chloro-5-hexynyloxy, and 6-bromo-5-hexynyloxy.
The (C1-C5 alkoxy)carbonyl represented by R10 may include, for example, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, tert-pentyloxycarbonyl, and 1-ethylpropyloxycarbonyl.
The C1-C3 alkylthio represented by R17 or R18 may include methylthio, ethylthio, propylthio, and isopropylthio.
The C1-C3 haloalkylthio represented by R17 or R18 may include, for example, trifluoromethylthio, difluoromethylthio, bromodifluoromethylthio, 2,2,2-trifluoroethylthio, 2-chloro- 1,1,2-trifluoroethylthio, 2-bromo-1,1,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, 2-chloroethylthio, 2-fluoroethylthio, 2-bromoethylthio, 1,1,2,2,2-pentafluoroethylthio, 3-fluoropropylthio, 3-chloropropylthio, 3-bromopropylthio, 2,2,3,3,3-pentafluoropropylthio, and 3,3,3-trifluoropropylthio.
The C1-C2 alkylsulfinyl represented by R17 or R18 may include methylsulfinyl or ethylsulfinyl.
The C1-C2 alkylsulfonyl represented by R17 or R18 may include methylsulfonyl and ethylsulfonyl.
The C1-C2 haloalkylsulfinyl represented by R17 or R18 may include, for example, trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl, and perfluoroethylsulfinyl.
The C1-C2 haloalkylsulfonyl represented by R17 or R18 may include, for example, trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl, and perfluoroethylsulfonyl.
The C1-C3 hydroxyalkyl represented by R17 or R18 may include hydroxymethyl, 2-hydroxyethyl, and 3-hydroxypropyl.
The C2-C4 alkoxyalkyl represented by R17 or R18 may include, for example, methoxymethyl, ethoxymethyl, propyloxymethyl, isopropyloxymethyl, 2-methoxyethyl, 1-methoxyethyl, 2-ethoxyethyl, 1-ethoxyethyl, 3-methoxypropyl, 2-methoxypropyl, 1-methoxypropyl, and 2-methoxy-1-methylethyl.
The C2-C4 alkylthioalkyl represented by R17 or R18 may include, for example, methylthiomethyl, ethylthiomethyl, propylthiomethyl, isopropylthiomethyl, 2-methylthioethyl, 1-methylthioethyl, 2-ethylthioethyl, 1-ethylthioethyl, 3-methylthiopropyl, 2-methylthiopropyl, 1-methylthiopropyl, and 2-methylthio-1-methylethyl.
The (C1-C2 alkyl)aminocarbonyl represented by R17 may include methylaminocarbonyl or ethylaminocarbonyl.
The di(C1-C2 alkyl)aminocarbonyl represented by R17 may include dimethylaminocarbonyl, N-methyl-N-ethylaminocarbonyl, or diethylaminocarbonyl.
The (C1-C6 alkoxy)carbonyl represented by R17 may include, for example, methoxycarbonyl, ethoxycarbonyl, n-propyloxycarbonyl, isopropyloxycarbonyl, n-butyloxycarbonyl, isobutyloxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, n-pentyloxycarbonyl, isopentyloxycarbonyl, neopentyloxycarbonyl, tert-pentyloxycarbonyl, 1-ethylpropyloxycarbonyl, n-hexyloxycarbonyl, isohexyloxycarbonyl, 2-ethylbutyloxycarbonyl, 1-methylpentyloxycarbonyl, 1-ethylbutyloxycarbonyl, 3-methylpentyloxycarbonyl, and 1,3-dimethylbutylcarbonyl.
The C1-C6 cycloalkenyl represented by R17 may include 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, or 3-cyclohexenyl.
The C3-C6 cycloalkyloxy represented by R17 may include cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, or cyclohexyloxy.
The C1-C6 cycloalkenyloxy represented by R17 may include 1-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy, 1-cyclohexenyloxy, 2-cyclohexenyloxy, or 3-cyclohexenyloxy.
The 3,3-dihalogeno-substituted-2-propenyl represented by R4 may include, for example, 3,3-dichloro-2-propenyl, 3,3-dibromo-2-propenyl, 3-bromo-3-chloro-2-propenyl, 3-chloro-3-fluoro-2-propenyl, and 3-bromo-3-fluoro-2-propenyl.
The C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl, which is represented by R6, R8, or R9, may include, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 2-methylcyclopentyl, 3-methylcyclopentyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 4-ethylcyclohexyl, 4-n-propylcyclohexyl, 4-isopropylcyclohexyl, and 4-tert-butylcyclohexyl.
The C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof, which is represented by R6, R8, or R9, may include, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropylethyl, (2-methylcyclopropyl)methyl, 2-(2-methylcyclopropyl)ethyl, 2-cyclopentylethyl, 3-cyclopentylpropyl, 2-cyclohexylethyl, and 3-cyclohexylpropyl.
The C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl, which is represented by R6, R8, or R9, may include, for example, 2-cyclopentenyl, 3-cyclopentenyl, 2-cyclohexenyl, 3-cyclohexenyl, 3,5,5-trimethyl-2-cyclohexenyl, and 3-methyl-2-cyclohexenyl.
The C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof, which is represented by R6, R8, or R9, may include, for example, (1-cyclopentenyl)methyl, (2-cyclopentenyl)methyl, (1-cyclohexenyl)-methyl, (2-cyclohexenyl)methyl, (3-cyclophexenyl)methyl, and 2-(3-cyclohexenyl)ethyl.
The halogen in the phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy, which is represented by R7, R5, R16, R17, R18, or R42, may include fluorine, chlorine, bromine, or iodine.
The C1-C4 alkyl in the phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy, which is represented by R7, R15, R16, R17, R18, or R42, may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl.
The C1-C3 haloalkyl in the phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy, which is represented by R7, R15, R16, R7, R18, or R42, may include, for example, trifluoromethyl, difluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, perfluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2-iodopropyl, and 2,3-dibromopropyl.
The C1-C3 alkoxy in the phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy, which is represented by R7, R15, R16, R17, R18, or R42, may include methoxy, ethoxy, n-propyloxy, or isopropyloxy.
The C1-C3 haloalkoxy in the phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy, which is represented by R7, R15, R16, R17, R10, or R42, may include, for example, trifluomethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 1-chloroethoxy, 1-bromothoxy, perfluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-tribromoethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2-dichloroethoxy, 2,2-dibromoethoxy, 3-fluoropropyloxy, 3-chloropropyloxy, 3-bromopropyloxy, 3-iodopropyloxy, 3,3,3-trifluoropropyloxy, 2,2,2,3,3,3-hexafluoropropyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2-fluoropropyloxy, 2-chloropropyloxy, 2-bromopropyloxy, 2-iodopropyloxy, and 2,3-dibromopropyloxy.
The halogen in the benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R7, R16, R17, or R42, may include fluorine, chlorine, bromine, or iodine.
The C1-C4 alkyl in the benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R7, R16, R17, or R42, may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl.
The C1-C3 haloalkyl in the benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R7, R16, R17, or R42, may include, for example, trifluoromethyl, difluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, perfluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2-iodopropyl, and 2,3-dibromopropyl.
The C1-C3 alkoxy in the benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R7, R16, R17, or R42, may include methoxy, ethoxy, n-propyloxy, or isopropyloxy.
The C1-C3 haloalkoxy in the benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R7, R16, R17, or R42, may include, for example, trifluoromethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 1-chloroethoxy, 1-bromoethoxy, perfluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-triluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-tribromoethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2-dichloroethoxy, 2,2-dibromoethoxy, 3-fluoropropyloxy, 3-chloropropyloxy, 3-bromopropyloxy, 3-iodopropyloxy, 3,3,3-trifluoropropyloxy, 2,2,2,3,3,3-hexafluoropropyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2-fluoropropyloxy, 2-chloropropyloxy, 2-bromopropyloxy, 2-iodopropyloxy, and 2,3-dibormopropyloxy.
The halogen in the phenoxy or benzyloxy optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R17, may include fluorine, chlorine, bromine, or iodine.
The C1-C4 alkyl in the phenoxy or benzyloxy optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R17, may include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and isobutyl.
The C1-C3 haloalkyl in the phenoxy or benzyloxy optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R17, may include, for example, trifluoromethyl, difluoromethyl, bromodifluoromethyl, 1-fluoroethyl, 1-chloroethyl, 1-bromoethyl, perfluoroethyl, 2-bromo-1,1,2,2-tetrafluoroethyl, 1,1,2,2-tetrafluoroethyl, 2-chloro-1,1,2-trifluoroethyl, 2-bromo-1,1,2-trifluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2-dichloroethyl, 2,2-dibromoethyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 3,3,3-trifluoropropyl, 2,2,2,3,3,3-hexafluoropropyl, 1,1,1,3,3,3-hexafluoro-2-propyl, 2-fluoropropyl, 2-chloropropyl, 2-bromopropyl, 2-iodopropyl, and 2,3-dibromopropyl.
The C1-C3 alkoxy in the phenoxy or benzyloxy optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R17, may include methoxy, ethoxy, n-propyloxy, or isopropyloxy.
The C1-C3 haloalkoxy in the phenoxy or benzyloxy optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof, which is represented by R17, may include, for example, trifluoromethoxy, bromodifluoromethoxy, 1-fluoroethoxy, 1-chloroethoxy, 1-bromoethoxy, perfluoroethoxy, 2-bromo-1,1,2,2-tetrafluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-chloro-1,1,2-trifluoroethoxy, 2-bromo-1,1,2-trifluoroethoxy, 2,2,2-trifluoroethoxy, 2,2,2-trichloroethoxy, 2,2,2-tribromoethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2-dichloroethoxy, 2,2-dibromoethoxy, 3-fluoropropyloxy, 3-chloropropyloxy, 3-bromopropyloxy, 3-iodopropyloxy, 3,3,3-trifluoropropyloxy, 2,2,2,3,3,3-hexafluoropropyloxy, 1,1,1,3,3,3-hexafluoro-2-propyloxy, 2-fluoropropyloxy, 2-chloropropyloxy, 2-bromopropyloxy, 2-iodopropyloxy, and 2,3-dibormopropyloxy.
The halogen in the methylenedioxy optionally substituted with halogen or C1-C3 alkyl, which is represented by R17 and which is formed from two adjacent R17""s combined together at their ends when b is 2 to 5, may include fluorine, chlorine, bromine, or iodine.
The C1-C3 alkyl in the methylenedioxy optionally substituted with halogen or C1-C3 alkyl, which is represented by R17 and which is formed from two adjacent R17""s combined together at their ends when b is 2 to 5, may include methyl, ethyl, n-propyl, and isopropyl.
The halogen in the ethylenedioxy optionally substituted with halogen or C1-C4 alkyl, which is represented by R17 and which is formed from two adjacent R17""s combined together at their ends when b is 2 to 5, may include fluorine, chlorine, bromine, or iodine.
The C1-C3 alkyl in the ethylenedioxy optionally substituted with halogen or C1-C3 alkyl, which is represented by R17 and which is formed from two adjacent R17""s combined together at their ends when b is 2 to 5, may include methyl, ethyl, n-propyl, and isopropyl.
R8 and R9, when combined together at their ends to form a saturated or unsaturated 5- or 6-membered ring containing zero to two oxygen or sulfur atoms in the ring thereof, represent tetramethylene optionally substituted with C1-C4 alkyl or halogen; pentamethylene optionally substituted with C1-C4 alkyl or halogen; butenylene optionally substituted with C1-C4 alkyl or halogen; pentenylene optionally substituted with C1-C4 alkyl or halogen; or pentadienylene optionally substituted with C1-C4 alkyl or halogen; examples of which are tetramethylene, 1-methyltetramethylene, 2-methyltetramethylene, 1,1-dimethyltetramethylene, 1,3-dimethyltetramethylene, pentamethylene, 1-methylpentamethylene, 2-methylpentamethylene, 3-methylpentamethylene, 3-ethylpentamethylene, 3-tert-butylpentamethylene, 1,1-dimethylpentamethylene, 1,5-dimethylpentamethylene, 1-chloropentamethylene, 1-methoxypentamethylene, 1-butenylene, 1-methyl-1-butenylene, 2-methyl- 1-butenylene, 1-pentenylene, 2-methyl-1-pentenylene, 3,3-dimethyl-1-pentenylene, 2-oxa-1-methyltetramethylene, 3-oxapentamethylene, 3-oxa-1,4-pentadienylene, 2-thiatetramethylene, 3-thiapentamethylene, 3, 3-dimethyl-2,4-dioxapentamethylene, and 2,4-dithiapentamethylene. In these groups, each methylene or methine linkage may be replaced with an oxygen or sulfur atom.
The C1-C6 cycloalkylene represented by E may include 1,2-cyclohexylene, 1,3-cyclohexylene, 1,4-cyclohexylene, 1,2-cyclopentylene, and 1,3-cyclopentylene.
The C1-C6 alkyl substituted with cyano, nitro, (C1-C4 alkoxy)carbonyl, C1-C4 alkylthio, or C1-C4 alkoxy, which is represented by R6, may include, for example, cyanomethyl, 1-cyanoethyl, 2-cyanoethyl, 3-cyanopropyl, nitromethyl, 1-nitroethyl, 1-methyl-1-nitroethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, isopropoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, methoxymethyl, ethoxymethyl, 1-methoxyethyl, 2-methoxyethyl, 2-ethoxyethyl, 2,2-dimethoxyethyl, 2,2-diethoxyethyl, 2,2-dimethoxypropyl, 2,2-diethoxypropyl, 3,3-dimethoxypropyl, 3,3-diethoxypropyl, 2,3-dimethoxypropyl, methylthiomethyl, 2-methylthioethyl, and 2,2-di(methylthio)ethyl.
In the case where h is 0 and i is 1 in A1-1, R22 and R7, when combined together at their ends to form trimethylene, tetramethylene, or pentamethylene, which is optionally substituted with C1-C3 alkyl, may include, for example, trimethylene, 1-methyltrimethylene, 2-methyltrimethylene, tetramethylene, 1-methyltetramethylene, 2-methyltetramethylene, and pentamethylene.
In the case where h is 0 and j is 1 in A1-2, A1-3, A1-4, A1-5, or A1-6, R22 and R7, when combined together at their ends to form trimethylene, tetramethylene, or pentamethylene, which is optionally substituted with C1-C3 alkyl, may include, for example, trimethylene, 1-methyltrimethylene, 2-methyltrimethylene, tetramethylene, 1-methyltetramethylene, 2-methyltetramethylene, and pentamethylene.
Preferred examples of the present compounds are as follows:
oxime compounds of formula (1) wherein X is X1;
oxime compounds of formula (1) wherein X is X1, and A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6;
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and Y and Z are both oxygen;
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and a is 0;
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and R1, R2, and R3 are independently halogen or C1-C3 alkyl;
oxime compounds of formula (1) wherein X is X1 and A1 is A1-1.
oxime compounds of formula (1) wherein X is X1, and A1 is A1-2, A1-3, A1-4, A1-5, or A1-6;
oxime compounds of formula (1) wherein A1 is A1-2, A1-3, A1-4, A1-5, or A1-6, and Q1 is oxygen.
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and R6 is C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C1-C6 haloalkenyl, C3-C6 alkynyl, or C3-C6 haloalkynyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C1-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C1-C6 alkyl substituted with cyano, nitro, (C1-C4 alkoxy)carbonyl, C1-C4 alkylthio, or C1-C4 alkoxy;
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and R6 is hydrogen.
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and R6 is triphenylmethyl, or T1-1, T1-2, or T1-3.
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and R6 is T1-4, T1-5, T1-6, or T1-7;
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and R7 is hydrogen, C1-C6 alkyl, C1-C3 haloalkyl, or C3-C6 cycloalkyl;
oxime compounds of formula (1) wherein A1 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6, and R7 is phenyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy,
or benzyl optionally substituted with halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy on the ring thereof.
oxime compounds of formula (1) wherein X is X1, R7 is hydrogen, C1-C6 alkyl, or C1-C3 haloalkyl,
A1 is A1-1, and
R6 is C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, or C3-C6 haloalkynyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof;
oxime compounds of formula (1) wherein X is X1, R7 is hydrogen, C1-C6 alkyl, or C1-C3 haloalkyl,
A1 is A1-1, and
R6 is T1-1 or T1-2;
oxime compounds of formula (1) wherein X is X1, R7 is hydrogen, C1-C6 alkyl, or C1-C3 haloalkyl,
A1 is A1-3, or A1 is A1-2 and k is an integer of 2 to 6, and
R6 is C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, or C3-C6 haloalkynyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof;
oxime compounds of formula (1) wherein X is X1, R7 is hydrogen, C1-C6 alkyl, or C1-C3 haloalkyl,
A1 is A1-3, or A1 is A1-2 and k is an integer of 2 to 6, and
R6 is T1-1 or T1-2;
oxime compounds of formula (1) wherein X is X1, R7 is hydrogen, C1-C6 alkyl, or C1-C3 haloalkyl,
A1 is A1-3, or A1 is A1-2 and k is an integer of 2 to 6, Q1 is oxygen, and
R6 is C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, or C3-C6 haloalkynyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or T1-1 or T1-2;
oxime compounds of formula (1) wherein R2 and R3 are independently chlorine or C1-C3 alkyl,
a is 0,
R4 is 3,3-dichloro-2-propenyl or 3,3-dibromo-2-propenyl,
Y and Z are both oxygen,
X is X1,
R6 is C1-C5 alkyl, C2-C4 haloalkyl, C3-C6 alkenyl, or C3-C6 haloalkenyl,
R7 is hydrogen, C1-C4 alkyl, or trifluoromethyl,
A1 is A1-1, R21 and R22 are both hydrogen, h is 0, and i is an integer of 3 to 5;
oxime compounds of formula (1) wherein R2 and R3 are independently chlorine or C1-C3 alkyl,
a is 0,
R4 is 3,3-dichloro-2-propenyl or 3,3-dibromo-2-propenyl,
Y and Z are both oxygen,
X is X1,
R6 is C1-C5 alkyl, C2-C4 haloalkyl, C3-C6 alkenyl, or C3-C6 haloalkenyl,
R7 is hydrogen, C1-C4 alkyl, or trifluoromethyl,
A1 is A1-2, R21, R22, R23, and R24 are all hydrogen, h is 0, Q1 is oxygen, j is 1, and k is an integer of 3 to 6;
oxime compounds of formula (1) wherein X is X1,
A1 is A1-1, R21 and R22 are both hydrogen, h is 0, i is an integer of 3 to 5,
Y and Z are both oxygen,
R2 and R3 are both chlorine,
a is 0,
R4 is 3,3-dichloro-2-propenyl,
R6 is isopropyl, isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,1,1,3,3,3-hexafluoro-2-propyl, or 3,3-dichloro-2-propenyl, and
R7 is hydrogen;
oxime compounds of formula (1) wherein X is X1,
A1 is A1-2, R21, R22, R23, and R24 are all hydrogen, h is 0, Q1 is oxygen, j is 1, k is an integer of 3 to 6,
Y and Z are both oxygen,
R2 and R3 are both chlorine,
a is 0,
R4 is 3,3-dichloro-2-propenyl,
R6 is isopropyl, isobutyl, sec-butyl, tert-butyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, 2,2,2-tribromoethyl, 1,1,1,3,3,3-hexafluoro-2-propyl, or 3,3-dichloro-2-propenyl, and R7 is hydrogen or methyl;
oxime compounds of formula (1) wherein X is X1, and A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and Y and Z are both oxygen;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and a is 0;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and R1, R2, and R3 are independently halogen or C1-C3 alkyl;
oxime compounds of formula (1) wherein A1 is A1-7;
oxime compounds of formula (1) wherein A1 is A1-8 and G2 is oxygen;
oxime compounds of formula (1) wherein A1 is A1-9 and Q1 is oxygen;
oxime compounds of formula (1) wherein A1 is A1-10, and Q1 and G2 are both oxygen;
oxime compounds of formula (1) wherein A1 is A1-11 and Q1 is oxygen;
oxime compounds of formula (1) wherein A1 is A1-12 and Q1 is oxygen;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and G1 is G1-1;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, G1 is G1-2, and Q2 is oxygen;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12,
R6 is hydrogen, C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, C3-C6 haloalkenyl, C3-C6 alkynyl, or C3-C6 haloalkynyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10, cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or more preferably, C1-C8 alkyl, C5-C6 haloalkyl, C3-C6 alkenyl, or C3-C6 haloalkenyl;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and
W is a benzene ring, a heterocyclic 6-membered ring containing at least oxygen, sulfur, or nitrogen atom, a heterocyclic 5-membered ring containing at least one oxygen, sulfur, or nitrogen atom, or any one of these rings substituted with one to four identical or different (R40)g2""s, wherein R40 is halogen, C1-C4 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, or C1-C3 haloalkoxy, and g2 is an integer of 1 to 4;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and
W is a benzene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyradine ring, a furan ring, a thiophene ring, a pyrrole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a pyrazole ring, an imidazole ring, or any one of these rings substituted with one to four identical or different (R40)g2""s;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and
W is a benzene ring, a pyridine ring, a pyridazine ring, or any one of these rings substituted with one to four identical or different (R40)g2""s;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and
W is a furan ring, a thiophene ring, a pyrrole ring, or any one of these rings substituted with one or four identical or different (R40)g2""s;
oxime compounds of formula (1) wherein A1 is A1-7, A1-8, A1-9, A1-10, A1-11, or A1-12, and
W is a benzene ring, 2,3-pyridinediyl, 2,4-pyridinediyl, 2,5-pyridinediyl, 2,6-pyridinediyl, 3,5-pyridinediyl, 3,4-pyridinediyl, 3,4-pyridazinediyl, 3,5-pyridazinediyl, 3,6-pyridazinediyl, or any one of these rings substituted with one to four identical or different (R40)g2""s;
oxime compounds of formula (1) wherein R2 and R3 are independently halogen or C1-C3 alkyl, R4 is 3,3-dichloro-2-propenyl,
a is O, Y and Z are both oxygen,
R6 is C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, or C3-C6 haloalkenyl, A1 is A1-7, G1 is G1-1, a1 is 0, W is 1,3-phenylene or 1,4-phenylene,
h and p are both 0, and
R19, R20, R25, R26, R29, and R30 are all hydrogen;
oxime compounds of formula (1) wherein R2 and R3 are independently halogen or C1-C3 alkyl, R4 is 3,3-dichloro-2-propenyl,
a is O, Y and Z are both oxygen,
R6 is C1-C8 alkyl, C2-C6 haloalkyl, C3-C6 alkenyl, or C3-C6 haloalkenyl,
A1 is A1-8, G1 is G1-1, a1 is 0, G2 is oxygen, W is 1,3-phenylene or 1,4-phenylene, h and p are both 0, and R19, R20, R25, R2, R29, and R30 are all hydrogen;
oxime compounds of formula (1) wherein X is X2;
oxime compounds of formula (1) wherein X is X2, and Y and Z are both oxygen;
oxime compounds of formula (1) wherein X is X2 and a is 0;
oxime compounds of formula (1) wherein X is X2, and R1, R2, and R3 are independently halogen or C1-C3 alkyl;
oxime compounds of formula (1) wherein A2 is A2-1;
oxime compounds of formula (1) wherein A2 is A2-2 and Q1 is oxygen;
oxime compounds of formula (1) wherein A2 is A2-3 and Q1 is oxygen;
oxime compounds of formula (1) wherein A2 is A2-4 and Q1 and Q3 are both oxygen;
oxime compounds of formula (1) wherein A2 is A2-5 and Q1 is oxygen;
oxime compounds of formula (1) wherein A2 is A2-6 and Q1 is oxygen;
oxime compounds of formula (1) wherein A2 is A2-7 or A2-9, and Q1 and Q2 are both oxygen;
oxime compounds of formula (1) wherein A2 is A2-8 or A2-10, and Q1 and Q2 are both oxygen;
oxime compounds of formula (1) wherein A2 is A2-5, and Q1 and Q2 are both oxygen;
oxime compounds of formula (1) wherein A2 is A2-6, and Q1, Q2, and Q3 are all oxygen;
oxime compounds of formula (1) wherein A2 is A2-1, h and p are both 0, and R19, R20, R25, R26, R29, and R30 are all hydrogen;
oxime compounds of formula (1) wherein A2 is A2-2, h and p are both 0, R19, R20, R25, R26, R27, R28, R31, and R32 are all hydrogen, and Q1 is oxygen;
oxime compounds of formula (1) wherein A2 is A2-3, h and p are both 0, R19, R20, R25, R26, R29, R30, R35, and R36 are all hydrogen, and Q2 is oxygen;
oxime compounds of formula (1) wherein A2 is A2-4, h and p are both 0, R19, R20, R25, R26, R29, R30, R35, and R36 are all hydrogen, and Q2 and Q3 are both oxygen;
oxime compounds of formula (1) wherein A2 is A2-5, h and p are both 0, R19, R20, R25, R26, R27, R28, R31, R32, R35, and R36 are all hydrogen, and Q1 and Q2 are both oxygen;
oxime compounds of formula (1) wherein A2 is A2-6, h and p are both 0, R19, R20, R25, R26, R27, R28, R31, R32, R35, and R36 are all hydrogen, and Q1, Q2, and Q3 are all oxygen;
oxime compounds of formula (1) wherein A2 is A2-7 or A2-9, h and p are both 0, R19, R20, R23, R24, R25, R26, R35, and R36 are all hydrogen, and Q1 and Q2 are both oxygen;
oxime compounds of formula (1) wherein A2 is A2-8 or A2-10, h and p are both 0, R9, R20, R2, R24, R25, R26, R35, and R36 are all hydrogen, and Q1 and Q2 are both oxygen;
oxime compounds of formula (1) wherein X is X2, and
R8 and R9 are independently hydrogen, C1-C11 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C10 alkoxyalkyl, C2-C10 alkylthioalkyl, or naphthyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or T2-1 or T2-2 of formula (4)

xe2x80x83wherein R17, D, R11, R12, b, and d are as defined above,
or a heterocyclic 6-membered ring, exclusive of pyridine ring, containing at least one oxygen, sulfur, or nitrogen atom, which heterocyclic 6-membered ring may be optionally substituted with one to three identical or different (R8)g""s, and R18 and g are as defined above,
or a heterocyclic 5-membered ring containing at least one oxygen, sulfur, or nitrogen atom, which heterocyclic 5-membered ring may be optionally substituted with one to three identical or different (R18)g""s, and R8 and g are as defined above,
or R8 and R9 are combined together at their ends to form a saturated or unsaturated 5- or 6-membered ring containing zero to two oxygen or sulfur atoms in the ring thereof;
oxime compounds of formula (1) wherein X is X2, and
R1 and R9 are independently hydrogen, C1-C11 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C10 alkoxyalkyl, C2-C10 alkylthioalkyl, or naphthyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,

xe2x80x83or T2-1 or T2-2 of formula (4)
wherein R17, D, R11, R12, b, and d are as defined above,
or 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, or 3-pyrrolyl, each of which heterocyclic groups may be optionally substituted with one to three identical or different (R18), wherein R18 and g are as defined above,
or R8 and R9 are combined together at their ends to form a saturated or unsaturated 5- or 6-membered ring containing zero to two oxygen or sulfur atoms in the ring thereof;
oxime compounds of formula (1) wherein X is X2, and
R8 and R9 are independently hydrogen, C1-C11 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C10 alkoxyalkyl, or C2-C10 alkylthioalkyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C5-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or T2-1 or T2-2 of formula (4)

xe2x80x83wherein R17, D, R11, R12, b, and d are as defined above,
or R8 and R9 are combined together at their ends to form a saturated or unsaturated 5- or 6-membered ring containing zero to two oxygen or sulfur atoms in the ring thereof;
oxime compounds of formula (1) wherein X is X2, and
R8 and R9 are independently hydrogen, C1-C11 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C10 alkoxyalkyl, or C2-C10 alkylthioalkyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C1-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or R8 and R9 are combined together at their ends to form a saturated or unsaturated 5- or 6-membered ring containing zero to two oxygen or sulfur atoms in the ring thereof; and
oxime compounds of formula (1) wherein X is X2, and
R8 and R9 are independently hydrogen, C1-C11 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C2-C10 alkoxyalkyl, or C2-C10 alkylthioalkyl,
or C3-C7 cycloalkyl optionally substituted with C1-C4 alkyl,
or C4-C10 cycloalkylalkyl optionally substituted with C1-C4 alkyl on the ring thereof,
or C1-C6 cycloalkenyl optionally substituted with C1-C4 alkyl,
or C6-C8 cycloalkenylalkyl optionally substituted with C1-C4 alkyl on the ring thereof.
Particularly preferred examples of the present compounds are as follows:
(187) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butanal O-isopropyloxime
(169) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal O-isopropyloxime
(188) 6-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)hexanal O-isopropyloxime
(26) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butanal O-tert-butyloxime
(16) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal O-tert-butyloxime
(134) 6-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)hexanal O-tert-butyloxime
(189) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butanal O-(2,2,2-trichloroethyl)oxime
(170) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal O-(2,2,2-trichloroethyl)oxime
(190) 6-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)hexanal O-(2,2,2-trichloroethyl)oxime
(24) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butanal O-(3,3-dichloro-2-propenyl)oxime
(17) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentanal O-(3,3-dichloro-2-propenyl)oxime
(76) 6-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)hexanal O-(3,3-dichloro-2-propenyl)oxime
(165) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde O-isopropyloxime
(152) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde O-isopropyloxime
(191) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butylxyacetone O-isopropyloxime
(172) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-isopropyloxime
(6) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde O-tert-butyloxime
(14) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde O-tert-butyloxime
(103) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetone O-tert-butyloxime
(104) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-tert-butyloxime
(167) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde O-(2,2,2-trichloroethyl)oxime
(160) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde O-(2,2,2-trichloroethyl)oxime
(192) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetone O-(2,2,2-trichloroethyl)oxime
(173) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-(2,2,2-trichloroethyl)oxime
(2) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetaldehyde O-(3,3-dichloro-2-propenyl)oxime
(15) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetaldehyde O-(3,3-dichloro-2-propenyl)oxime
(46) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxyacetone O-(3,3-dichloro-2-propenyl)oxime
(47) 5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyloxyacetone O-(3,3-dichloro-2-propenyl)oxime
(329) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)methylbenzaldehyde O-sec-butyloxime
(314) 4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)methylbenzaldehyde O-t-butyloxime
(355) 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde O-sec-butyloxime
(357) 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde O-allyloxime
(358) 4-(2-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)ethyl)benzaldehyde O-(3,3-dichloro-2-propenyl)oxime
(338) 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)benzaldehyde O-n-propyloxime
(339) 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)benzaldehyde O-isopropyloxime
(340) 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)benzaldehyde O-sec-butyloxime
(291) 4-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)benzaldehyde O-t-butyloxime
(293) 4xe2x80x2-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)acetophenone O-ethyloxime
(318) 4xe2x80x2-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)propiophenone O-ethyloxime
(297) 4xe2x80x2-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxy)acetophenone O-ethyloxime
(310) 4xe2x80x2-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxy)acetophenone O-n-propyloxime
(315) 4-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyloxy)bezaldehyde O-isopropyloxime
(391) 4xe2x80x2-(3-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)propyloxy)-2,2,2-trifluoroacetophenone O-ethyloxime
(529) 4-(trifluoromethyl)benzaldehyde O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)oxime
(531) 4xe2x80x2-(trifluoromethyl)acetophenone O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)oxime
(545) trimethylacetaldehyde O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyl)oxime
(559) 3,3-dimethyl-2-butanone O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyl)oxime
(562) 3,3-dimethyl-2-butanone O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)oxime
(563) 4-methyl-2-pentanone O-(4-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)butyl)oxime
(564) 4-methyl-2-pentanone O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyl)oxime
(582) 3-methyl-2-butanone O-(5-(2,6-dichloro-4-(3,3-dichloro-2-propenyloxy)phenoxy)pentyl)oxime
The above numbers preceding the compound names are also used below for designating the present compounds.
The present compounds can be produced, for example, by the following production processes A to M.
Production process A (the compounds of formula (1) wherein X is X1 and R6 is hydrogen are excluded)
This is the production process in which a compound of formula (15)

werein R1, R2, R3, a, X, Y, and Z are as defined above, with the proviso that when X is X1, R6 is not hydrogen, is reacted with a compound of formula (16)
Lxe2x80x94R4
wherein R4 is as defined above and L is halogen (e.g., chlorine, bromine, iodine), mesyloxy, or tosyloxy.
The reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (15).
The reaction temperature, although it can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C., is more preferably in the range of xe2x88x925xc2x0 C. to the boiling point of the solvent used in the reaction or 100xc2x0 C.
The molar ratio of the starting materials and base to be used in the reaction may be suitably selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process B (for the present compounds wherein Y is oxygen, with the proviso that when X is X1, R6 is not hydrogen)
This is the production process in which the compound of formula (15) wherein Y is oxygen is reacted with an alcohol compound of formula (17)
HOxe2x80x94R4
wherein R4 is as defined above.
The reaction is preferably effected in the presence of an appropriate dehydrating agent and, if necessary, in an inert solvent.
The dehydrating agent which can be used may include, for example, dicyclohexylcarbodiimide, dialkyl (e.g., C1-C4) azodicarboxylate (e.g., diethylazodicarboxylate, and diisopropylazodicarboxylate)-trialkyl (e.g., C1-C2) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine) systems.
The solvent which can be used may include, for example, hydrocarbons such as benzene, xylene, and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene.
The reaction temperature can be usually selected in the range of xe2x88x9220xc2x0 C. to 200xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of the starting materials and base to be used in the reaction may be suitably selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process C (for the present compounds wherein Y and Z are both oxygen, with the proviso that when X is X1, R6 is not hydrogen)
This is the production process in which a compound of formula (18)

wherein R1, R2, R3, R4, and a are as defined above, is reacted with a compound of formula (19)
xe2x80x83Xxe2x80x94L
wherein X and L are as defined above, with the proviso that when X is X1, R6 is hydrogen.
The reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (18).
The reaction temperature, although it can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C., is more preferably in the range of xe2x88x925xc2x0 C. to the boiling point of the solvent used in the reaction or 100xc2x0 C.
The molar ratio of the starting materials and base to be used in the reaction may be suitably selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process D (for the present compounds wherein Y and Z are both oxygen, with the proviso that when X is X1, R6 is not hydrogen)
This is the production process in which a compound of formula (18) is reacted with a compound of formula (20)
Xxe2x80x94OH
wherein X is as defined above, with the proviso that when X is X1, R6 is not hydrogen.
The reaction is preferably effected in the presence of an appropriate dehydrating agent and, if necessary, in an inert solvent.
The dehydrating agent which can be used may include, for example, dicyclohexylcarbodiimide, dialkyl (e.g., C1-C4) azodicarboxylate (e.g., diethylazodicarboxylate, and diisopropylazodicarboxylate)-trialkyl (e.g., C1-C20) phosphine or triarylphosphine (e.g., triphenylphosphine, trioctylphosphine, tributylphosphine) systems.
The solvent which can be used may include, for example, hydrocarbons such as benzene, xylene, and toluene; ethers such as diethyl ether, diisopropyl ether, tetrahydrofuran, and dioxane; and halogenated hydrocarbons such as carbon tetrachloride, dichloromethane, chlorobenzene, and dichlorobenzene.
The reaction temperature can be usually selected in the range of xe2x88x9220xc2x0 C. to 200xc2x0 C. or the boiling point of a solvent used in the reaction.
The molar ratio of starting materials and dehydrating agent to be used in the reaction may be suitably selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process E (for the present compounds wherein X is X1)
This is the production process in which a hydroxylamine compound of formula (21)
R6Oxe2x80x94NH2
20 wherein R1 is as defined above, or a sat thereof, is reacted with a carbonyl compound of formula (22)

wherein R1, R2, R3, R4, R7, A1, Y, Z, and a are as defined above.
The reaction can be effected in an inert solvent and, if necessary, in the presence of a base or an acid.
The solvent which can be used may include, for example, alcohols such as methanol and ethanol; ethers such as diethyl ether, tetrahydrofuran, and dioxane; acetic acid; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. The amount of base to be used, if necessary, in the reaction is preferably 1 mole or more relative to 1 mole of the hydroxylamine compound of formula (21). The organic bases such as triethylamine and pyridine can serve both as the base and as the solvent, when the reaction is effected with them in large excess relative to the hydroxylamine compound of formula (21).
The acid which can be used may include, for example, hydrochloric acid, sulfuric acid, and p-toluenesulfonic acid. The acid can be used in the reaction at a catalytic amount ranging from 0.01 to 1 equivalent relative to the carbonyl compound of formula (22).
The hydroxylamine compound as the starting material, although it can be used as such in the reaction, is usually used in the form of an inorganic acid salt, such as hydrochloride or sulfate.
The reaction temperature, although it can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C., is more preferably in the range of 0xc2x0 C. to the boiling point of the solvent used in the reaction or 60xc2x0 C.
The molar ratio of the starting materials and reagents to be used in the reaction may be freely selected; however, it is favorable that the reaction of the carbonyl compound of formula (22) and the hydroxylamine compound of formula (21) or a salt thereof is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process F (for the present compounds wherein X is X1, with the proviso that R6 is not hydrogen, T1-4, T1-5, T1-6, or T1-7)
This is the production process in which a compound of formula (23)
R6xe2x80x94L
wherein R6 and L are as defined above, with the proviso that R6 is not hydrogen, T1-4, T1-5, T1-6, or T1-7, is reacted with a compound of formula (24)

wherein R1, R2, R3, R4, R7, A1, Y, Z, and a are as defined above (i.e., the present compound wherein X is X1 and R6 is hydrogen).
The reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (24).
The reaction temperature, although it can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C., is more preferably in the range of xe2x88x925xc2x0 C. to the boiling point of the solvent used in the reaction or 100xc2x0 C.
The molar ratio of the starting materials and base to be used in the reaction may be freely selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process G (for the present compounds wherein Y and Z are both oxygen, X is X1, A1 is A1-8, and e1 is 0, with the proviso that R6 is not hydrogen)
This is the production process in which a compound of formula (25)

wherein R1, R2, R3, R4, R19, R20, R23, R24, R25, R26, R27 R28, R29, R30, a h, j, p, u, v, and L are as defined above, is reacted with a compound of formula (26)

wherein R6, R7, G1, and W are as defined above, Q4 is oxygen, sulfur, or NR39, and R39 is as defined above.
The reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (25).
The reaction temperature can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C.
The molar ratio of the starting materials and base to be used in the reaction may be suitably selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process H (for the present compounds wherein Y and Z are both oxygen, X is X2, A2 is A2-4, and e1 is 0)
This is the production process in which a compound of formula (27)

wherein R1, R2, R3, R4, R19, R20, R23, R24, R25, R26, R27, R28, R29, R30, j, h, t, p, m, a, and L are as defined above, is reacted with compound U5-1, U5-2, or U6-3 of formula (28)

wherein R8, R9, R35, R36, R40, g1, h1, i1, R, V, Q2, and Q4 are as defined above.
The reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (27).
The reaction temperature can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C.
The molar ratio of the starting materials and base to be used in the reaction may be freely selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process I (for the present compounds wherein X is X2)
This is the production process in which an O-substituted hydroxylamine compound of formula (29)

wherein R1, R2, R3, R4, A2, Z, Y, and a are as defined above, or a salt thereof, is reacted with a carbonyl compound of formula (30)

wherein R8 and R9 are as defined above.
The reaction can be effected in an inert solvent and, if necessary, in the presence of a base.
The solvent which can be used may include, for example, alcohols such as methanol and ethanol; ethers such as diethyl ether, tetrahydrofuran, and dioxane; pyridine; and water. The carbonyl compound of formula (30) may also be used as the solvent. If necessary, these solvents may also be used in admixture.
The base which can be used may include, for example, triethylamine, pyridine, and sodium acetate.
The O-substituted hydroxylamine compound as the starting material is usually used in the form of an inorganic acid salt such as hydrochloride.
The reaction temperature is usually in the range of 0xc2x0 C. to 150xc2x0 C.
The molar ratio of the starting materials and reagents to be used in the reaction may be suitably selected; however, it is preferred that the reaction of the carbonyl compound of formula (30) and the O-substituted hydroxylamine compound of formula (29) or a salt thereof is effected at the equimolar ratio or a ratio close thereto. The amount of base to be used, if necessary, in the reaction is preferably 1 mole or more relative to 1 mole of the compound of formula (29).
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process J (for the present compounds wherein X is X2)
This is the production process in which a compound of formula (31)

wherein R8 and R9 are as defined above, is reacted with a compound of formula (32)

wherein R1, R2, R3, R4, A2, Z, Y, a, and L are as defined above.
The reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, sodium carbonate, potassium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In necessary, catalysts such as ammonium salts (e.g., triethylbenzylammonium chloride) may be added to the reaction system in an amount of 0.01 to 1 mole relative to 1 mole of the compound of formula (31).
The reaction temperature can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C.
The molar ratio of the starting materials and base to be used in the reaction may be freely selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process K (for the compounds wherein X is X1 and R6 is T1-4, T1-5, or T1-7)
This is the production process in which a compound of formula (33)

wherein J and R15 are as defined above, and L1 is chlorine or bromine (when R6 is T1-4),
or a compound of formula (34)

wherein R15 is as defined above (when R6 is T1-4),
or a compound of formula (35)

wherein J, R16, R42, and L1 are as defined above (when R6 is T1-5),
or a sulfonyl halide compound of formula (36)

wherein R15 and L1 are as defined above (when R6 is T1-7), is reacted with a compound of formula (24).
The reaction is preferably effected in the presence of an appropriate base and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; and water. If necessary, these solvents may also be used in admixture.
The base which can be used may include hydroxides of alkali metals or alkaline earth metals, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide; carbonates of alkali metals or alkaline earth metals, such as lithium carbonate, potassium carbonate, sodium carbonate, and calcium carbonate; hydrides of alkali metals or alkaline earth metals, such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride; alkoxides (e.g., C1-C4) of alkali metals, such as sodium methoxide, sodium ethoxide, and potassium tert-butoxide; and organic bases such as triethylamine and pyridine. In particular, organic bases such as triethylamine or pyridine are preferably used.
The reaction temperature, although it can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction or 150xc2x0 C., is more preferably in the range of xe2x88x925xc2x0 C. to the boiling point of the solvent used in the reaction or 50xc2x0 C.
The molar ratio of the starting materials and base to be used in the reaction may be freely selected; however, it is favorable that the reaction is effected with the compound of formula (33), (34), (35), or (36) and the base in an amount of 1 to 5 moles, respectively, relative to 1 mole of the compound of formula (24).
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process L (for the present compounds wherein X is X1 and R6 is T1-6)
This is the production process in which an isocyanate compound or an isothiocyanate compound of formula (37)
R16xe2x80x94Nxe2x95x90C=J
wherein J and R16 are as defined above, is reacted with a compound of formula (24).
The reaction is effected, if necessary, in the presence of an appropriate catalyst and in an inert solvent.
The solvent which can be used may include ketones such as acetone, methyl ethyl ketone, and cyclohexanone; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, dioxane, and dialkyl (e.g., C1-C4) ether (e.g., diethyl ether, diisopropyl ether); polar solvents such as N,N-dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, sulforane, acetonitrile, and nitromethane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; and hydrocarbons such as toluene, benzene, and xylene. If necessary, these solvents may also be used in admixture.
As the catalyst, for example, bases such as triethylamine, pyridine, and sodium acetate, or acids such as aluminum chloride, hydrogen chloride, and boron trifluoride ether complex (BF3.(C2H5)2O), can be used.
The reaction temperature, although it can be usually selected in the range of xe2x88x9220xc2x0 C. to the boiling point of a solvent used in the reaction, is more preferably in the range of xe2x88x925xc2x0 C. to the boiling point of the solvent used in the reaction.
The molar ratio of the starting materials be used in the reaction may be freely selected; however, it is favorable that the reaction is effected at the equimolar ratio or a ratio close thereto.
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
Production process M (for the present compounds wherein X is X1 and R6 is tert-butyl)
This is the production process in which isobutene (CH2xe2x95x90C(CH3)) is reacted with a compound of formula (24).
The reaction is effected in the presence of an appropriate acid catalyst and in an inert solvent.
The solvent which can be used may include, for example, hydrocarbons such as toluene, benzene, and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; ethers such as 1,2-dimethoxyethane, tetrahydrofuran, and dioxane, dialkyl (e.g., C1-C4) ethers (e.g., diethyl ether, diisopropyl ether); and esters such as ethyl acetate. If necessary, these solvents may also be used in admixture.
The acid catalyst which can be used may include, for example, inorganic acids such as hydrochloric acid, hydrobromic acid, perchloric acid, sulfuric acid, nitric acid, and phosphoric acid; and organic acids such as trifluoroacetic acid, trichloroacetic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, and camphorsulfonic acid. In particular, sulfuric acid is preferably used.
The reaction temperature, although it can be usually selected in the range of xe2x88x9250xc2x0 C. to 50xc2x0 C. or the boiling point of a solvent used in the reaction, is usually in the range of 0xc2x0 C. to 30xc2x0 C.
The molar ratio of the starting materials to be used in the reaction may be suitably selected; however, the reaction is preferably effected with the use of isobutene in an amount of 1 mole or more relative to 1 mole of the compound of formula (24).
After completion of the reaction, the reaction mixture is subjected to ordinary post-treatments such as extraction with an organic solvent and/or concentration. Thus, the desired present compounds can be isolated. If necessary, further purification may be carried out by an ordinary technique such as chromatography, distillation, or recrystallization.
For the present compounds, there may exist optical isomers based on the presence of at least one asymmetric carbon atom, and the optical isomers having biological activity, whether they are either in (+)-form or in (xe2x88x92)-form, and their mixtures at any ratio are, of course, included within the scope of the present invention. Furthermore, there may exist geometrical isomers based on the presence of at least one double bond, and the geometrical isomers having biological activity, whether they are either in cis-form or in trans-form, and their mixtures at any ratio are, of course, included within the scope of the present invention.
The compounds of formula (12), which are useful as the intermediates for the production of the present compounds, also have insecticidal/acaricidal activity and can therefore be formulated or used as the active ingredients of insecticidal/acaricidal agents, in the same manner as the case of the present compounds.
The specific examples of the present compounds are shown below; however, the present compounds are not limited to these examples.




























p













In the above formulae, (R1)a, R2, R3, and M2 are as defined in Table 1 below, and R6is as defined in Tables 2 to 19 below.
In Table 7, xe2x80x94(CR11R12)dxe2x80x94 is bonded at the left side to the benzene ring.
In Table 8, xe2x80x94(CR11R12)dxe2x80x94 is bonded at the left side to the pyridine ring.
In Table 9, xe2x80x94(CR11R12)dxe2x80x94 is bonded at the left side to the pyridine ring.
In Table 10, xe2x80x94(CR11R12)dxe2x80x94 is bonded at the left side to the pyridine ring.
In Table 11, xe2x80x94(CR11R12)exe2x80x94Oxe2x80x94(CR13R14)fxe2x80x94 is bonded at the left side to the benzene ring.
In Table 12, xe2x80x94(CR11R12)exe2x80x94Oxe2x80x94(CR13R14)fxe2x80x94 is bonded at the left side to the pyridine ring.
In Table 13, xe2x80x94(CR11R12)exe2x80x94Oxe2x80x94(CR13R14)fxe2x80x94 is bonded at the left side to the pyridine ring.
In Table 14, xe2x80x94(CR11R12)exe2x80x94Oxe2x80x94(CR13R14)fxe2x80x94 is bonded at the left side to the pyridine ring.


In the above formulae, R8 and R9 are as defined in Tables 20 to 47.
The following will describe various processes for producing the inter. mediates in the production of the present compounds.
The compounds of formula (15) as the intermediates for the production of the present compounds can be produced, for example, according to the following schemes I to VI.

wherein all the variables are as defined above, with the proviso that R6 is not hydrogen.

wherein all the variable are as defined above, with the proviso that R6 is not hydrogen.

wherein all the variable are as defined above, with the proviso that R6 is not hydrogen.

wherein all the variable are as defined above, with the proviso that R6 is not hydrogen.

wherein TBDMSCl is tert-butyldimethylsillyl chloride, Z1 is oxygen or sulfur, and the other variables are as defined above, with the proviso that R6 is not hydrogen.

wherein all the variables are as defined above, with the proviso that R6 is not hydrogen.
The compounds of formula (18) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme VII.

wherein all the variables are as defined above.
The halide compounds of formula (16) and alcohol compounds of formula (17), both as the intermediates for the production of the present compounds, are commercially available or can be produced, for example, according to the publications: J. Org. Chem., 56, 1037-1041 (1991); Izvest. Akad. Nauk S.S.S.R., Otdel. Khim. Nauk, 1960, 447-451 [CA (Chemical Abstracts) vol. 54, 22344d]; and Doklady Akad. Nauk S.S.S.R. 132, 606-608 (1960) [CA (Chemical Abstracts) vol. 54, 22331h], or according to the following scheme VIII.

wherein L1 is chlorine or bromine, L2 is mesyloxy or tosyloxy, and M is halogen.
The compounds of formula (19) or (20) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme IX or X.

wherein R51 is a protecting group for alcohols, such as benzoyl or acetyl,
Q10 is oxygen, sulfur, or NR33 wherein R33 is as defined above,
A3 is A1-1, A1-2, A1-3, A1-4, A1-5, or A1-6,
G3 is G3-2, G3-3, G3-4, G3-5, or G3-6 of formula (38) when A1 is A1-2, A1-3, A1-4, A1-5, or A1-6,
G3-2: xe2x80x94(CR23R24)kxe2x80x94 (when A1 is A1-2)
G3-3: xe2x80x94(CR23R24)mxe2x80x94CR25xe2x95x90CR26xe2x80x94(CR27R28)nxe2x80x94 (when A1 is A1-3)
G3-4: xe2x80x94(CR23R24)mxe2x80x94Cxe2x89xa1Cxe2x80x94(CR25R26)nxe2x80x94 (when A1 is A1-4)
G3-5: xe2x80x94(CR23R24)pxe2x80x94Exe2x80x94(CR25R26)qxe2x80x94 (when A1 is A1-5)
G3-6: xe2x80x94(CR23R24)rxe2x80x94Q2xe2x80x94(CR25R26)sxe2x80x94 (when A1 is A1-6)
wherein all the variables are as defined above, and the other variables are as defined above.

wherein all the variables are as defined above.
The compounds of formula (22) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XI, XII, XIII, XIV, or XV

wherein Y1 is oxygen or NH, R52 is a protecting group for the hydroxyl group of phenol or for the amino group of aniline, such as benzoyl, acetyl, or tert-butylmethylsillyl (TBDMS), and the other variables are as defined above.

wherein R53 is methyl or ethyl, R54 is a protecting group for the hydroxyl group of phenol, such as benzoyl or acetyl, and the other variables are as defined above.

wherein all the variables are as defined above.

wherein R53 is methyl or ethyl, R55 is a protecting group for the hydroxyl group of phenol, such as benzyl, DIBAL means diisobutylaluminum hydride, and the other variables are as defined above.

wherein R55 is a protecting group for the hydroxyl group of phenol, such as benzyl, R56 is acetyl or benzoyl, PCC means pyridinium chlorocromate, and the other variables are as defined above.
The compounds of formula (21) as the intermediates for the production of the present compounds are commercially available or can be produced, or example, according to the following scheme XVI.

wherein L3 is a leaving group such as halogen, hydroxysulfonyloxy, or 2,4,6-trimethylbenzenesulfonyloxy, and the other variables are as defined above.
The compounds of formula (33), (34), (35), (36), or (37), as the intermediates for the production of the present compounds, are commercially available or can be produced by the methods widely known in the art or by the methods as described in the publications: [compounds of formula (33) wherein J is sulfur] J. Org. Chem., 3, 1284 (1965); [compounds of formula (35) wherein J is oxygen] J. Am. Chem. Soc., 1, 714 (1959); [compounds of formula (35) wherein J is sulfur] Justus Liebigs Ann. Chem., 690, 123 (1954).
The compounds of formula (19) or (20) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XVII.

wherein all the variables are as defined above.
The compounds of formula (39) can be produced, for example, according to the following schemes XVIII-1 to XVIII-9.

wherein R101 is L or Q4H, Q4 is oxygen, sulfur, or NR34, R34 is hydrogen or C1-C3 alkyl, R102 is a protecting group for alcohols, such as benzoyl, A11 is A11-7, A11-8, A11-9, A11-10, A11-11, or A11-12 of formula (40)
A11-7: xe2x80x94(CR19R20)txe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)uxe2x80x94(CR27xe2x95x90CR28)pxe2x80x94(CR29R30)jxe2x80x94
A11-8: xe2x80x94G2xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR26R26)uxe2x80x94(CR27xe2x95x90CR28)Pxe2x80x94(CR29R30)vxe2x80x94
A11-9: xe2x80x94(CR19R20)txe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)jxe2x80x94Q1xe2x80x94(CR27R28)vxe2x80x94(CR29xe2x95x90CR30)pxe2x80x94(CR31R32)wxe2x80x94
A11-10: xe2x80x94G2xe2x80x94(CR19R20)jxe2x80x94(CR23xe2x95x90CR24)hxe2x80x94(CR25R26)vxe2x80x94Q1xe2x80x94(CR27R28)wxe2x80x94(CR29xe2x95x90CR30)pxe2x80x94(CR31R32)xxe2x80x94
A11-11: xe2x80x94(CR19R20)txe2x80x94Q1xe2x80x94(CR23R24)hxe2x80x94Exe2x80x94(CR25R26)pxe2x80x94
A11-12: xe2x80x94(CR19R20)txe2x80x94Q1xe2x80x94(CR23R24)jxe2x80x94Cxe2x89xa1Cxe2x80x94(CR25R26)mxe2x80x94
and the other variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein ail the variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein Q5 is oxygen, sulfur, or N33, and the other variables are as defined above.
The compounds of formula (25) as the intermediates for the production of the present compounds can be produced, for example, according to scheme XIV.

where all the variables are as defined above.
The compounds of formula (26) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XX.

wherein Q7 is oxygen or sulfur, and the other variables are as defined above.
The compounds of formula (21) as the intermediates for the production of the present compounds are commercially available or can be produced, for example, according to the following scheme XXI.

wherein R103 and R104 are C1-C3 alkyl, and the other variables are as defined above, with the proviso that R6 is not hydrogen.
The carbonyl compounds of formula (22) as the intermediates for the production of the present compounds can be produced, for example, according to the following schemes XXI-1 to XXII-5.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein R105 is methyl or ethyl, W1 is a benzene ring or a heterocyclic ring containing no xe2x80x94NHxe2x80x94 linkage in the ring thereof, and the other variables are as defined above.

wherein R108 is methyl or ethyl, or two R108""s are combined together at their ends to form ethylene or trimethylene, and the other variables are as defined above.

wherein all the variables are as defined above.
The compounds of formula (24) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XXIII.

wherein all the variables are as defined above.
Some of the compounds of formula (41), (42), or (43) are commercially available or can be produced according to the following schemes XXIV-1 to XXIV-4.

wherein R106 is methyl or ethyl, R107 is C1-C6 alkyl, C3-C6 cycloalkyl, or phenyl or benzyl, each of which may be optionally substituted with C1-C4 alkyl or C1-C3 alkoxy, and the other variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.
The starting compounds of formula (47)
R109xe2x80x94W1xe2x80x94R110
wherein R109 and R110 are L1, Q4H, CHO, CH(OR108)2, CO2H, CO2R105, COCH3, or CH2L1, and the other variables are as defined above, which are used in the schemes XXII-3, XXII-4, XXII-5, XXIV-1, XXIV-2, XXIV-3, and XXIV-4, and other compounds are commercially available or can be produced, for example, by the methods as described in the following publications.
In the case where W1 is a pyridazine ring:
J. Heterocyclic Chem., 5, 845 (1968);
Monatschefte fur Chem., 110, 365 (1979), etc.
In the case where W1 is a pyrimidine ring:
Justus Liebigs Ann. Chem., 684, 209 (1965);
J. Heterocyclic Chem., 28, 1281 (1991);
Chem. Ber., 97, 3407 (1964);
J. Chem. Soc., 1965, 5467;
Aust. J. Chem., 19, 2321 (1966), etc.
In the case where W1 is a pyradine ring:
J. Org. Chem., 54, 640 (1089) etc.
In the case where W1 is an oxazole ring:
J. Org. Chem., 57, 4797 (1992) etc.
In the case where W1 is an isoxazole ring:
Chem. Pharm. Bull., 14, 92 (1966);
Chem. Pharm. Bull., 14, 1277 (1966);
Chem. Pharm. Bull., 19, 46 (1971);
J. Chem. Res. Synop., 1994, 116;
Synthesis, 1976, 992, etc.
In the case where W1 is a thiazole ring:
J. Am. Chem. Soc., 72, 5221 (1950) etc.
In the case where W1 is an isothiazole ring:
J. Chem. Soc., 1959, 3061 etc.
In the case where W1 is an imidazole ring:
Tetrahedron Lett., 26, 1915 (1985) etc.
In the case where W1 is a pyrazole ring:
Chem. Ber., 112, 1712 (1979);
Chem. Ber., 116, 1520 (1983);
JP-A 63-185964/1988;
Tetrahedron, 29, 441 (1973);
J. Chem. Soc., Chem. Commun., 1969, 66;
J. Org. Chem., 35, 3451 (1970);
Chem. Ber., 103, 2356 (1970), etc.
The compounds of formula (19) or (20) wherein X is X2, as the intermediates for the production of the present compounds, can be produced, for example, according to the following scheme XXV.

wherein L3 is halogen (e.g., chlorine, bromine, iodine), mesyloxy, or tosyloxy, R151 is a protecting group for alcohols, such as described in PROTECTIVE GROUPS IN ORGANIC SYNTHESIS, T. W. Greene, P. G. M. Wuts, A WILEY-INTERSCIENCE PUBLICATION, JOHN WILEY and SONS, INC., pp. 10-142; e.g., benzoyl, and the other variables are as defined above.
The compounds of formula (48) or (49) in the scheme XXV can be produced, for example, according to the following schemes XXVI to XXXXIII.

wherein all the variables are as defined above.

wherein L4 is halogen (e.g., chlorine, bromine, iodine), mesyloxy, or tosyloxy, Q8 is oxygen, sulfur, or NR33, R33 is hydrogen or C1-C3 alkyl, and the other variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein Q9 is oxygen, sulfur, or NR34, R34 is hydrogen or C1-C3 alkyl, and the other variables are as defined above.

wherein R152 is a protecting group for alcohols (as described in PROTECTIVE GROUPS IN ORGANIC SYNTHESIS, T. W. Greene, P. G. M. Wuts, A WILEY-INTERSCIENCE PUBLICATION, JOHN WILEY and SONS, INC., pp. 10-142; as a protecting group selectively removable for R151, for example, when R151 is benzoyl, R152 is tetrahydropyranyl), and the other variables are as defined above.

wherein R153 is a protecting group (as described in PROTECTIVE GROUPS IN ORGANIC SYNTHESIS, T. W. Greene, P. G. M. Wuts, A WILEY-INTERSCIENCE PUBLICATION, JOHN WILEY and SONS, INC., pp. 143-170 and 277-405; for example, when Q4 is oxygen, R113 is benzoyl), and the other variables are as defined above.

wherein all the variables are defined above.

wherein all the variables are as defined above.


wherein L5 is halogen (e.g., chlorine, bromine, iodine), mesyloxy, or tosyloxy, and the other variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.


wherein all the variables are as defined above.

wherein all the variables are as defined above.


wherein all the variables are as defined above.

wherein all the variables are as defined above.

wherein all the variables are as defined above.
The compounds of formula (27) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XXXXIV.

wherein all the variables are as defined above.
The compounds of formula (28) as the intermediates for the production of the present compounds can be produced, for example, according to the following schemes XXXXV to XXXXVII.

wherein all the variables are as defined above.

wherein all the variables are as defined above.

where all the variable are as defiend above.
The compounds of formula (29) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XXXXVIII.

wherein all the variables are as defined above.
The compounds of formula (32) as the intermediates for the production of the present compounds can be produced, for example, according to the following scheme XXXXIX.

wherein all the variables are as defined above.
The harmful insects and harmful ticks and mites, against which the present compounds exhibit controlling activity, may include, for example, the following:
The present compounds are satisfactorily effective for the control of various noxious insects, mites and ticks, examples of which are as follows:
Hemiptera:
Delphacidae such as Laodelphax stiiatellus, Nilaparvata lugens, and Sogatella furcifera, Deltocephalidae such as Nephotettix cincticeps and Empoasca onukii, Aphididae such as Aphis gossypii and Myzus persicae, Pentatomidae, Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, and Bemisia argentifolii, Coccidae, Tingidae, Psyllidae, etc.
Lepidoptera:
Pyralidae such as Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilalis, and Parapediasia teterrella, Noctuidae such as Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Trchoplusia spp., Heliothis spp., Helicoverpa spp. and Earias spp., Pieridae such as Pieris rapae crucivora, Tortricidae such as Adoxophyes orana fasciata, Grapholita molesta, and Cydia pomonella, Carposinidae such as Carposina niponensis, Lyonetiidae such as Lyonetia clerkella, Gracillariidae such as Phyllonorycter ringoniella, Phyllocnistidae such as Phyllocnistis citrella, Yponomeutidae such as Plutella xylostella, Gelechiidae such as Pectinophora gossypiella, Arctiidae, Tineidae, etc.
Diptera:
Calicidae, Aedes spp., Anopheles spp., Chironomidae, Muscidae, Callphoridae, Sarcophagidae, Anthomyiidae, Cecidomyiidae, Agromyzidae, Tephritidae, Drosophilidae, Psychodidae, Simuliidae, Tabanidae, Stomoxyidae, etc.
Coleoptera:
Chrysomelidae, Scarabaeidae, Curculionidae, Attelabidae, Coccinellidae, Cerambycidae, Tenehrionidae, etc.
Thysanoptera:
Thripidae such as Thrips spp., e.g., Thrips palmi, Frankliniella spp., e.g., Frankliniella occidentalis, Sciltothrips spp., e.g., Sciltothrips dorsalis, and Phlaeothenipidae, etc.
Hymenoptera:
Tenthredinidae, Formicidae, Vespidae, etc.
Dictyoptera:
Blattidae, Blattellidae, etc.
Orthoptera:
Acrididae, Gryllotalpidae, etc.
Aphaniptera:
Purex irritans etc.
Anoplura:
Pediculus humanus capitis etc.
Isoptera:
Termitidae etc.
Acaiina:
Tetranychidae such as Tetranychus spp. and Panonychus spp., Tarsonemidae, Eriophyidae, Acaridae, Ixodidae, etc.
The present compounds are also effective for the control of various noxious insects, mites and ticks with resistance to conventional insecticides or acaricides.
When the present compounds are used as the active ingredients of insecticidal/acaricidal agents, they may be used as such without addition of any other ingredients. The present compounds are, however, usually mixed with solidcarriers, liquid carriers, gaseous carriers, or baits, and if necessary, with surfactants and other auxiliaries, and formulated into various forms, such as oil sprays, emulsifiable concentrates, wettable powders, flowables, granules, dusts, aerosols, fumigants (e.g., foggings), or poison baits.
Each of these formulations may usually contain at least one of the present compounds as an active ingredient in an amount of 0.01% to 95% by weight.
The solid carrier which can be used in the formulation may include, for example, fine powder or granules of clay materials such as kaolin clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, Fubasami clay, and acid clay; various kinds of talc, ceramics, and other inorganic minerals such as sericite, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica; and chemical fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride.
The liquid carrier may include, for example, water; alcohols such as methanol and ethanol; ketones such as acetone and methyl ethyl ketone; hydrocarbons such as hexane, cyclohexane, kerosene, and light oil; esters such as ethyl acetate and butyl acetate; nitrites such as acetonitrile and isobutyronitrile; ethers such as diisopropyl ether and dioxane; acid amides such as N,N-dimethylformamide and N,N-dimethylacetamide; halogenated hydrocarbons such as dichloromethane, trichloroethane, and carbon tetrachloride; dimethyl sulfoxide; and vegetable oils such as soybean oil and cottonseed oil.
The gaseous carrier or propellant may include, for example, Freon gas, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide.
The surfactant may include, for example, alkyl sulfates, alkyl sulfonates, alkyl arylsulfonates, alkyl aryl ethers and their polyoxyethylene derivatives, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
The auxiliaries such as fixing agents or dispersing agents may include, for example, casein, gelatin, polysaccharides such as starch, gum arabic, cellulose derivatives, and alginic acid, lignin derivatives, bentonite, sugars, and synthetic water-soluble polymers such as polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acid.
The stabilizer may include, for example, PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (mixtures of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, surfactants, fatty acids, and their esters.
The base material for used in poison baits may include, for example, bait materials such as grain powder, vegetable oils, sugars, and crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; preservatives such as dehydroacetic acid; substances for preventing erroneous eating, such as red pepper powder; attractant flavors such as cheese flavor or onion flavor.
The formulations thus obtained are used as such or after diluted with water. Furthermore, they may be used in admixture with or separately but simultaneously with other insecticides, nematocides, acaricides, bactericides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil conditioners and/or animal.
The insecticide, nematocide and/or acaricide which can be used may include, for example, organophosphorus compounds such as Fenitrothion [O,O-dimethyl O-(3-methyl-4-nitrophenyl)phosphorothioate], Fenthion [O,O-dimethyl O-(3-methyl-4-(methylthio)phenyl)phophorothioate], Diazinon [O,O-diethyl-O-2-isopropyl-6-methylpyrimidin-4-ylphosphorothioate], Chlorpyriphos [O,O-diethyl-O-3,5,6-trichloro-2-pyridylphosphorothioate], Acephate [O,S-dimethylacetylphosphoramidothioate], Methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-ylmethyl O,O-dimethylphosphorodithioate], Disulfoton [O,O-diethyl S-2-ethylthioethylphosphorothioate], DDVP [2,2-dichlorovinyldimethylphosphate], Sulprofos [O-ethyl O-4-(methylthio)phenyl S-propyl phosphorodithioate], Cyanophos [O-4-cyanophenyl O,O-dimethylphosphorothioate], Dioxabenzofos [2-methoxy-4H-1,3,2-benzodioxaphosphinine-2-sulfide], Dimethoate [O,O-dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphate], Phenthoate [ethyl 2-dimethoxyphosphinothioylthio(phenyl)acetate], Malathion [diethyl(dimethoxyphosphinothioylthio)succinate], Trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate], Azinphos-methyl [S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl-methyl 0,0-dimethylphosphorodithioate], Monocrotophos [dimethyl (E)-1-methyl-2-(methylcarbamoyl)vinylphosphate], Ethion [O,O,Oxe2x80x2,Oxe2x80x2-tetraethyl S,Sxe2x80x2-methylenebis(phosphorodithioate)], and Profenofos [O-4-bromo-2-chlorophenyl O-ethyl S-propyl phosphorothioate]; carbamate compounds such as BPMC (2-sec-butylphenylmethylcarbamate), Benfuracarb [ethyl N-[2,3-di-hydro-2,2-dimethylbenzofuran-7-yloxycarbonyl(methyl)aminothio]-N-isopropyl-p-alaninate], Propoxur [2-isopropoxyphenyl N-methylcarbamate], Carbosulfan [2,3-dihydro-2,2-dimethyl-7-benzo[b]furanyl N-dibutylaminothio-N-methylcarbamate], Carbaril [1-naphthyl-N-methylcarbamate], Methomyl [S-methyl-N-[(methylcarbamoyl)oxy]thioacetimidate], Ethiofencarb [2-(ethylthiomethyl)phenylmethylcarbamate], Aldicarb [2-methyl-2-(methylthio)-propionaldehyde O-methylcarbamoyloxime], Oxamyl [N,N-dimethyl-2-methylcarbamoyloxyimino-2-(methylthio)acetamide], Fenothiocarb [S-4-phenoxybutyl]-N,N-dimethylthiocarbamate], Thiodicarb [3,7,9,13-tetramethyl-5,11-dioxa-2,8, 14-trithia-4,7,9,12-tetraazapentadeca-3,12-diene-6,10-dione], and Alanycarb [ethyl (Z)-N-benzyl-N-{[methyl(1-methylthioethylideneaminooxycarbonyl)amino]thio}-xcex2-alaninate]; pyrethroid compounds such as Etofenprox [2-(4-ethoxyphenyl)-2-methylpropyl-3-phenoxybenzylether], Fenvalerate [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2-(4-chlorophenyl)-3-methylbutyrate], Esfenvalerate [(S)-xcex1-cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate], Fenpropathrin [(RS)-xcex1-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate], Cypermethrin [(RS)-xcex1-cyano-3-phenoxybenzyl (1RS,3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Permethrin [3-phenoxybenzyl (1RS, 3RS)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate], Cyhalothrin [(RS)-xcex1-cyano-3-phenoxy-benzyl (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate], Deltamethrin [(S)-xcex1-cyano-3-phenoxybenzyl (1R,3R)-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate], Cycloprothrin [(RS)-xcex1-cyano-3-phenoxybenzyl (RS)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropanecarboxylate], Fluvalinate (xcex1-cyano-3-phenoxybenzyl N-(2-chloro-xcex1,xcex1,xcex1-trifluoro-p-tolyl)-D-valinate), Bifenthrin (2-methylbiphenyl-3-yl-methyl) (Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-cyclopropanecarboxylate), Acrinathrin [(S)-xcex1-cyano-(3-phenoxyphenyl)-methyl [1R-{1xcex1(S*), 3xcex1(Z)}]-2,2-dimethyl-3-[3-oxo-3-(2,2,2-trifluoro-1-(tri-fluoromethyl)ethoxy-1-propenyl)cyclopropanecarboxylate], 2-methyl-2-(4-bromodifluoromethoxyphenyl)propyl (3-phenoxybenzyl) ether, Traromethrin [(S)-xcex1-cyano-3-phenoxylbenzyl (1R,3R)-3-[(lxe2x80x2RS)(1xe2x80x2,1xe2x80x2,2xe2x80x2,2xe2x80x2-tetrabromoethyl)]-2,2-dimethylcyclopropanecarboxylate], and Silafluofen [4-ethoxylphenyl [3-(4-fluoro-3-phenoxyphenyl)propyl]dimethylsilane]; thiadiazine derivatives such as Buprofezin (2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-thiadiazin-4-one; nitroimidazolidine derivatives such as Imidacloprid [1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylidenamine]; Nereistoxin derivatives such as Cartap [S,Sxe2x80x2-(2-dimethylaminotrimethylene)bis(thiocarbamate)], Thiocyclam [N,N-dimethyl-1,2,3-trithian-5-ylamine], and Bensultap [S,Sxe2x80x2-2-dimethylaminotrimethylene di(benzenethiosulfonate)]; N-cyanoamidine derivatives such as acetamiprid [N-cyano-Nxe2x80x2-methyl-Nxe2x80x2-(6-chloro-3-pyridyl-methyl)acetamidine]; chlorinated hydrocarbon compounds such as Endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a,6,9,9a-hexahydro-6,9-methano-2,4,3-benzodioxathiepinoxide], xcex3-BHC (1,2,3,4,5,6-hexachlorocyclohexane), and 1,1-bis(chlorophenyl)-2,2,2-trichloroethanol; benzoylphenylurea compounds such as Chlorfluazuron [1-(3,5-dichloro-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)phenyl)-3-(2,6-difluorobenzoyl)urea], Teflubenzuron [1-(3,5-dichloro-2,4-difluorophenyl)-3-(2,6-difluorobenzoyl)urea], and Fulphenoxron [1-(4-(2-chloro-4-trifluoromethylphenoxy)-2-fluorophenyl)-3-(2,6-difluorobenzoyl)-urea]; formamidine derivatives such as Amitraz [N,Nxe2x80x2-[(methylimino)-dimethylidine]-di-2,4-xylidine], and Chlordimeform [Nxe2x80x2-(4-chloro-2-methylphenyl)-N,N-dimethylmethanimidamide]; thiourea derivatives such as Diafenthiuron [N-(2,6-diisopropyl-4-phenoxyphenyl)-Nxe2x80x2-tert-butylcarbodi-imide]; Bromopropylate [isopropyl 4,4xe2x80x2-dibromobenzylate], Tetradifon [4-chlorophenyl 2,4,5-trichlorophenylsulfone], Quinomethionate [S,S-6-methylquinoxaline-2,3-diyldithiocarbonate], Propargate [2-(4-tert-butylphenoxy)cyclohexyl prop-2-yl sulfite], Fenbutatin oxide [bis[tris(2-methyl-2-phenylpropyl)tin]oxide], Hexythiazox [(4RS,5RS)-5-(4-chlorophenyl)-N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], Chlofentezine [3,6-bis(2-chlorophenyl)-1,2,4,5-tetrazine], Pyridaben [2-tert-butyl-5-(4-tert-butylbenzylthio)-4-chloropyridazin-3(2H)-one], Fenpyroximate [tert-butyl (E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)methyleneaminooxymethyl]-benzoate], Tebfenpyrad [N-4-tert-butylbenzyl]-4-chloro-3-ethyl-1-methyl-5-pyrazolecarboxamide], polynactin complexes [e.g., tetranactin, dinactin, trinactin]; Milbemectin, Avermectin, Ivermectin, Azadilactin [AZAD], Pyrimidifen [5-chloro-N-[2-{4-(2-ethoxyethyl)-2,3-dimethylphenoxy}ethyl]-6-ethylpyrimidin-4-amine], Chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethylpyrrole-3-carbonitrile], Tebfenozide [N-tert-butyl-Nxe2x80x2-(4-ethylbenzoyl)-3,5-dimethylbenzohydrazide], and phenylpyrazole derivatives.
When the present compounds are used as the active ingredients of insecticidal/acaricidal agents for agriculture, the application amount thereof is usually in the range of 0.1 to 100 g per 10 ares. When they are used after diluted with water in the case of emulsifiable concentrates, wettable powders, flowables, or similar formulations, the application concentration thereof is usually in the range of 1 to 10,000 ppm. In the case of granules, dusts, or similar formulations, they are applied as such formulations without any dilution. When the present compounds are used as the active ingredients of insecticidal/acaricidal agents for epidemic prevention, they are usually applied after diluted with water to a typical concentration of 0.1 to 500 ppm in the case of emulsifiable concentrates, wettable powders, flowable, or similar formulations; or they are applied as such in the case of oil sprays, aerosols, fumigants, poisonous baits, or similar formulations.
The application amount and concentration may vary depending upon the conditions including types of formulations, times, places and methods of application, kinds of noxious insects, mites and ticks, and degree of damage, and they can be increased or decreased without limitation to the above range.